Photoexcited Palladium-Catalyzed Synthesis of Chiral Allenes from Alkynes via Isomerization and Deracemization Sequence

被引:0
|
作者
Song, Changhua [1 ]
Yu, Shouyun [1 ]
机构
[1] Nanjing Univ, Chem & Biomed Innovat Ctr ChemBIC, Sch Chem & Chem Engn, State Key Lab Analyt Chem Life Sci,Jiangsu Key Lab, Nanjing 210023, Peoples R China
来源
ACS CATALYSIS | 2024年 / 14卷 / 21期
基金
中国国家自然科学基金;
关键词
alkynes; allenes; deracemization; isomerization; palladium; CYCLIZATION REACTIONS;
D O I
10.1021/acscatal.4c04956
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A photoexcited palladium-catalyzed synthesis of chiral allenes from alkynes via a sequence of isomerization and deracemization is disclosed. This method offers an efficient and cost-effective approach to produce a wide range of chiral allenes with good enantioselectivities and yields (up to 98% yield and 99% ee). The use of readily available and stable alkynes as starting materials simplifies experimental procedures and broadens the scope of the chiral allene synthesis. DBU plays a crucial dual role in this reaction to effectively facilitate the isomerization of alkynes to allenes and enhance the palladium-catalyzed deracemization under visible light excitation, both of which are vital for the success of the process.
引用
收藏
页码:15997 / 16002
页数:6
相关论文
共 50 条
  • [21] Catalytic synthesis of allenes via isomerization of alkynes under phase-transfer catalyzed conditions
    Oku, M
    Arai, S
    Katayama, K
    Shiori, T
    SYNLETT, 2000, (04) : 493 - 494
  • [22] Palladium-catalyzed asymmetric synthesis of axially chiral allenes: A synergistic effect of dibenzalacetone on high enantioselectivity
    Ogasawara, M
    Ikeda, H
    Nagano, T
    Hayashi, T
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (09) : 2089 - 2090
  • [23] Synthesis of alpha-pyrones via palladium-catalyzed annulation of internal alkynes
    Han, XJ
    Larock, RC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 214 : 360 - ORGN
  • [24] Synthesis of isoquinoline and pyridine heterocycles via palladium-catalyzed iminoannulation of internal alkynes
    Roesch, KR
    Larock, RC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 : U505 - U505
  • [25] Synthesis of Multisubstituted Allenes, Furans, and Pyrroles via Tandem Palladium-Catalyzed Substitution and Cycloisomerization
    Ryu, Taekyu
    Eom, Dahan
    Shin, Seohyun
    Son, Jeong-Yu
    Lee, Phil Ho
    ORGANIC LETTERS, 2017, 19 (03) : 452 - 455
  • [26] Rapid Access to Nitrogenous Heterobicycles via RhIII-Catalyzed Isomerization from Alkynes to Allenes
    Nakamura, Itaru
    Takeda, Keisuke
    Sato, Yoshinori
    Terada, Masahiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (32) : 7686 - 7688
  • [27] Synthesis of silirenes by palladium-catalyzed transfer of silylene from siliranes to alkynes
    Palmer, WS
    Woerpel, KA
    ORGANOMETALLICS, 1997, 16 (22) : 4824 - 4827
  • [28] PALLADIUM-CATALYZED SYNTHESIS OF DIENIC ALPHA-AMINO-ACIDS FROM ALLENES
    KOPOLA, N
    FRIESS, B
    CAZES, B
    GORE, J
    TETRAHEDRON LETTERS, 1989, 30 (30) : 3963 - 3966
  • [29] Synthesis of β- and γ-carbolines by the palladium-catalyzed iminoannulation of internal alkynes
    Zhang, HM
    Larock, RC
    ORGANIC LETTERS, 2001, 3 (20) : 3083 - 3086
  • [30] Synthesis of indenes by the palladium-catalyzed carboannulation of internal alkynes
    Zhang, DH
    Yum, EK
    Liu, ZJ
    Larock, RC
    ORGANIC LETTERS, 2005, 7 (22) : 4963 - 4966